Planning the split
I’ve reached the point at work where I need to leave. It’s not a good situation for me, I’m not adding much value to the company, and it’s taking a toll on me physically and emotionally. So I need to get my act together, update my resume and CV, contact friends (it always amazes me how ‘small’ Silicon Valley really is), and make sure I’m financially covered when I announce I’m leaving. Hopefully that will be sometime early next year.
Leaving a company is somewhat like a divorce, and fortunately many of the things the company must do is dictated by law or in the different plans it has in place. Does anyone know of a checklist somewhere so I can make sure I’m planning for everything? I know HR will go over everything with me, but I’d rather have everything planned in advance.
The things that come to mind that I’ll need to check or plan:
- Health coverage (I’m familiar with how COBRA works, but I still need to read our different plans’ fine print)
- 401K (I’m planning on leaving it where it is for now—I like the funds we have to choose from)
- Vacation pay (I’ve accrued about a month and a half worth of time off that I’ll get when I leave)
- Options (I don’t have too many that are in the money, but some of our plans require exercise within 60 days, some give you a year, so I’ll need to be clear on which options fall under which bracket. I'd rather not let anything expire that's in the money, and give our stock some time to increase for those that allow the time.)
- Supplemental insurance—the company offered this last year and I enrolled. I think the policy is mine when I leave and will just need to make the payments directly instead of through payroll.
- Term life policies—I have a feeling I won’t be able to continue some of these, but I’d love to be able to if I can
- Flex spending health account—plan to file for reimbursement the same or a less amount than is withheld during the piece of 2007 I’m here so I don’t have to pay back when I leave. I'm sure when you get into pre-tax vs. post-tax dollars here, things can get messy.
Anything else I need to review? I hate to say it but it’s been so long since I changed companies that I’ve forgotten most of the paperwork and planning involved. I’ve been lucky in that the current company has provided me with great opportunities to move up and develop, but now it’s time to go.
Leaving a company is somewhat like a divorce, and fortunately many of the things the company must do is dictated by law or in the different plans it has in place. Does anyone know of a checklist somewhere so I can make sure I’m planning for everything? I know HR will go over everything with me, but I’d rather have everything planned in advance.
The things that come to mind that I’ll need to check or plan:
- Health coverage (I’m familiar with how COBRA works, but I still need to read our different plans’ fine print)
- 401K (I’m planning on leaving it where it is for now—I like the funds we have to choose from)
- Vacation pay (I’ve accrued about a month and a half worth of time off that I’ll get when I leave)
- Options (I don’t have too many that are in the money, but some of our plans require exercise within 60 days, some give you a year, so I’ll need to be clear on which options fall under which bracket. I'd rather not let anything expire that's in the money, and give our stock some time to increase for those that allow the time.)
- Supplemental insurance—the company offered this last year and I enrolled. I think the policy is mine when I leave and will just need to make the payments directly instead of through payroll.
- Term life policies—I have a feeling I won’t be able to continue some of these, but I’d love to be able to if I can
- Flex spending health account—plan to file for reimbursement the same or a less amount than is withheld during the piece of 2007 I’m here so I don’t have to pay back when I leave. I'm sure when you get into pre-tax vs. post-tax dollars here, things can get messy.
Anything else I need to review? I hate to say it but it’s been so long since I changed companies that I’ve forgotten most of the paperwork and planning involved. I’ve been lucky in that the current company has provided me with great opportunities to move up and develop, but now it’s time to go.

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